P-TERT-PENTYLPHENOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H16O
Molecular Weight	164.2441
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(C)(C)C1=CC=C(O)C=C1

InChI

InChIKey=NRZWYNLTFLDQQX-UHFFFAOYSA-N

InChI=1S/C11H16O/c1-4-11(2,3)9-5-7-10(12)8-6-9/h5-8,12H,4H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C11H16O
Molecular Weight	164.2441
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19233257 | https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/290845/scho0208bnqr-e-e.pdf

4-tert-Pentylphenol (4-tert-Amylphenol) is used to make phenolic resins (novolaks and resoles), which are used in paints and varnishes and as printing ink resins. The ethoxylated novolaks are used as oil field demulsifiers. Because of the high cost of 4-tert-pentylphenol, which is related to the high cost of the starting material, many of the resin applications have been reformulated using 4-tertbutylphenol. The substance is also used as a germicide in cleaning solutions, although it is being replaced by quaternary ammonium salts. Kegley et al. (2007) confirm that both the substance and its potassium and sodium salts are antimicrobial or fungicidal active ingredients of several disinfectant products that are currently registered with the US authorities. It appears that some of these products are used in animal husbandry, including the control of highly infectious diseases such as avian influenza (US EPA, 2007d). 4-tert-Amylphenol was used as an esterogen receptor (ER) ligand.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19233257 \| https://www.ncbi.nlm.nih.gov/pubmed/12765246 \| https://www.ncbi.nlm.nih.gov/pubmed/12504345	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bronchial spasm 78 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14353164	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of phthalate esters and alkylphenols on steroidogenesis in human adrenocortical H295R cells.	2001 Jul	21782564
Determination of phenolic disinfectant agents in commercial formulations by liquid chromatography.	2001 May-Jun	11417646
[Study on para-derivative of phenol as enhancers of chemiluminescence].	2002 Dec	12914157
Fish full life-cycle testing for the weak estrogen 4-tert-pentylphenol on medaka (Oryzias latipes).	2003 Jul	12836973
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
Ecotoxicological evaluation of the biocidal agents sodium o-phenylphenol, sodium o-benzyl-p-chlorophenol, and sodium p-tertiary amylphenol.	2005 Feb	15546637
Effects of 4-tert-pentylphenol on the gene expression of P450 11beta-hydroxylase in the gonad of medaka (Oryzias latipes).	2005 Jan 26	15642637
Impurities in a lyophilized formulation of BMS-204352: identification and role of sanitizing agents.	2006	16749531
Development of chronic tests for endocrine active chemicals. Part 1. An extended fish early-life stage test for oestrogenic active chemicals in the fathead minnow (Pimephales promelas).	2006 May 10	16483677
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
In vitro cytotoxicity assessment of the biocidal agents sodium o-phenylphenol, sodium o-benzyl-p-chlorophenol, and sodium p-tertiary amylphenol using established fish cell lines.	2006 Oct	16678383
A proteomic (SELDI-TOF-MS) approach to estrogen agonist screening.	2007 Jan	16917070
Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications.	2010 Feb 15	19913605
Effects of a weak oestrogenic active chemical (4-tert-pentylphenol) on pair-breeding and F1 development in the fathead minnow (Pimephales promelas).	2010 May 10	20106537
Single-laboratory validation of a method for the determination of phenols and phenates in disinfectant formulations by liquid chromatography with UV detection.	2010 May-Jun	20629411

Patents

Sample Use Guides

In Vivo Use Guide

Acute oral toxicity tests have been conducted with 4-tert-pentylphenol in the rat. In the more recent study, conducted to OECD guidelines, five male and five female animals were given 4-tert-pentylphenol in corn oil by gavage at a limit dose of 2,000 mg/kg.

Route of Administration: Oral

In Vitro Use Guide

For the agonist assay, 4-tert-Pentylphenol diluted in DMSO was added to the wells to final concentrations of 10 uM, 1 uM, 100 nM, 10 nM, 1 nM, 100 pM, and 10 pM, in quadruplicate. A stable transfected cell line, hERa/HeLa, was used.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:10:48 GMT 2023` Edited by `admin` on `Fri Dec 15 15:10:48 GMT 2023`
Record UNII	6NP9LYK846
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

P-TERT-PENTYLPHENOL

Common Name

English

P-TERT-AMYLPHENOL

Common Name

English

PENTAPHEN

Systematic Name

English

4-(1,1-DIMETHYLPROPYL)PHENOL [HSDB]

Common Name

English

2-METHYL-2-P-HYDROXYPHENYLBUTANE

Common Name

English

NSC-403672

Code

English

AMYLPHENOL [MART.]

Common Name

English

P-TERT-PENTYLPHENOL [MI]

Common Name

English

4-TERT-AMYLPHENOL

Systematic Name

English

AMYLPHENOL

Systematic Name

English

AMYLPHENOL, P-TERT-

Common Name

English

TERTIARY AMYL PHENOL

Common Name

English

4-(2-METHYLBUTAN-2-YL)PHENOL

Systematic Name

English

4-(1,1-DIMETHYLPROPYL)PHENOL

Systematic Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

64101